13 Chapter

HYDROCARBONS

Trend
Analysis of NEET and AIIMS (Year 2010-2018)

8
7
6
AIPMT /NEET
5
Number of Questions

AIIMS
4
3
2
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2010 2011 2012 2013 2014 2015 2016 2017 2018
Year

Trend
Analysis of JEE Main and BITSAT (Year 2010-2018)

4
JEE Main
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Chapter Utility Score (CUS)

Exam Weightage Important Concepts Difficulty Level CUS (Out of 10)
NEET 4 Substitution reaction in alkanes,
AIIMS 5 conformation of ethane, addition 4/5 8.4
reaction in alkenes, ozonolysis,
JEE Main 4 Friedel craft reaction, electrophilic
BITSAT 3 substitution reaction
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HYDROCARBONS 167
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Exercise 1 : Topic-wise MCQs

Topic 1: Alkanes 12. Liquid hydrocarbons can be converted to a mixture of

gaseous hydrocarbons by :
1. The number of chain isomers possible for the hydrocarbon
(a) oxidation
C5H12 is
(b) cracking
(a) 1 (b) 2 (c) 3 (d) 4 (c) distillation under reduced pressure
2. Name of the given compound - (d) hydrolysis
CH3 13. n-Hexane isomerises in presence of anhydrous aluminium
CH3 chloride and hydrogen chloride gas to give
(a) 2-Methyl pentane (b) 3-Methyl pentane
CH3 (c) Both (a) and (b) (d) Neither (a) nor (b)
14. How many conformations are possible for ethane ?
CH3 (a) 2 (b) 3 (c) infinite (d) one
(a) 2, 3-diethyl heptane (b) 5-ethyl-6-methyl octane 15. Spatial arrangements of atoms which can be converted into
(c) 4-ethyl-3-methyl octane (d) 3-methyl-4-ethyl octane one another by rotation around a C–C single bond are called
3. Which of the following statements is false for isopentane/ (a) Stereoisomers (b) Tautomers
(a) It has three CH3 groups (c) Optical isomers (d) Conformers
(b) It has one CH2 group 16. Which of the following statements are correct regarding
(c) It has one CH group structure of methane ?
(d) It has a carbon which is not bonded to hydrogen (i) Methane has tetrahedral structure.
4. Molecular formula of which of the following alkane can exist (ii) The bond angle between all H – C – H bonds is 109.5°.
in more than one structure ? (iii) The carbon atom is sp2 hybridized.
(a) CH4 (b) C2H6 (c) C3H8 (d) C4H10 (iv) C – C and C – H bond lengths are 154 pm and 112 pm
respectively.
5. The reaction,
(a) (i), (ii) and (iii) (b) (i), (iii) and (iv)
CH 3 - Br + 2Na + Br – CH 3 ® the product, is called (c) (i), (ii) and (iv)(d) (i), (ii), (iii) and (iv)
(a) Wurtz reaction (b) Perkin’s reaction 17. In the preparation of alkanes from hydrogenation of alkenes
(c) Aldol condensation (d) Levit reaction and alkynes, finely divided catalysts are used which of the
6. Pure methane can be produced by following statement(s) is/are correct regarding these
(a) Wurtz reaction catalysts
(b) Kolbe’s electrolytic method (i) Platinum and palladium catalyse the reaction at room
(c) Soda-lime decarboxylation temperature.
(d) Reduction with H2 (ii) Nickel catalyses the reaction at relatively higher
7. Sodium salts of carboxylic acids on heating with soda lime temperature and pressure.
give alkanes containing _______ than the carboxylic acid. (iii) Platinum and palladium catalyse the reaction at higher
(a) one carbon more (b) one carbon less temperature.
(c) two carbon less (d) Either (a) or (b) (a) (i) and (iii) (b) (i) and (ii)
8. In the free radical chlorination of methane, the chain initiating (c) (ii) and (iii) (d) (i) only
step involves the formation of 18. Which of the following statements are correct ?
(a) chlorine free radical (b) hydrogen chloride (i) The rate of reactivity of alkanes with halogens is
(c) methyl radical (d) chloromethyl radical. F2 > Cl2 > Br2 > I2.
9. Which one of the following gives only one monochloro (ii) Rate of replacement of hydrogens of alkanes is
derivative? 3° > 2º > 1°
(a) n-Hexane (b) 2-MMethylpentane (iii) Fluorination of alkanes is a very slow process.
(c) 2, 3-Dimethylpentane (d) neo-Pentane (iv) Iodination of alkanes is too violent to be controlled.
10. Photochemical halogenation of alkane is an example of (a) (i), (ii) and (iii) (b) (i) and (ii)
(a) electrophilic substitution (c) (ii) and (iii) (d) (i) and (iv)
(b) electrophilic addition 19. Which of the following statements are correct ?
(c) nucleophilic substitution (i) Decomposition reaction of higher alkanes into smaller
(d) free radical substitution fragments by the application of heat is called pyrolysis.
11. Complete combustion of CH4 gives : (ii) Pyrolysis and cracking are different processes.
(a) CO2 + H2O (b) CO2 + H2 (iii) Dodecane on pyrolysis gives a mixture of heptane and
(c) COCl2 (d) CO + CO2 + H2O pentene.
HYDROCARBONS 169

(iv) Pyrolysis follows free radical mechanism. (a) Assertion is correct, reason is correct; reason is a
(a) (i), (ii) and (iii) (b) (i), (ii) and (iv) correct explanation for assertion.
(c) (i), (iii) and (iv) (d) (ii) and (iv) (b) Assertion is correct, reason is correct; reason is not a
20. Which of the following statement(s) is/are correct ? correct explanation for assertion
(i) Alkanes can have infinite number of conformations by (c) Assertion is correct, reason is incorrect
rotation around a C – C single bonds. (d) Assertion is incorrect, reason is correct.
(ii) Rotation around C – C single bond is completely free. 26. A hydrocarbon A on chlorination gives B which on heating
(iii) Rotation is hindered by a small energy barrier of with alcoholic potassium hydroxide changes into another
1-20 kJ mol–1 due to torsional strain. hydrocarbon C. The latter decolourises Baeyer's reagent
(a) (i) and (ii) (b) (i) and (iii) and on ozonolysis forms formaldehyde only. A is
(c) (ii) and (iii) (d) Only (iii) (a) Ethane (b) Butane
21. Which of the following statements are correct ? (c) Methane (d) Ethene
(i) Stability of conformation is affected due to torsional 27. Which of the following compounds can yield only one
strain. monochlorinated product upon free radical chlorination?
(ii) Magnitude of torsional strain depends upon the angle (a) Propane (b) 2, 2-Dimethylpropane
of rotation about C – C bond. (c) 2-Methylpropane (d) n-Butane
(iii) Eclipsed form has least torsional strain.
Topic 2: Alkenes
(iv) Staggered form has maximum torsional strain.
(a) (i) and (iii) (b) (i) and (ii) 28. The restricted rotation about carbon-carbon double bond
(c) (iii) and (iv) (d) (i) and (iv) in 2- butene is due to
22. Match the columns (a) overlap of one s- and one sp2-hybridized orbitals
Column-I Column-II (b) overlap of two sp2-hybridized orbitals
(A) CH2 = CH2 ® CH3 – CH3 (p) H2, Zn, H+ (c) overlap of one p-and one sp2-hybridized orbitals
(B) CH3Cl ® CH4 (q) NaOH, CaO (d) sideways overlap of two p-orbitals
(C) CH3Br ® CH3CH3 (r) H2, Pt/Pd 29. IUPAC name of the following compound will be
(D) CH3COONa ® CH4 (s) Na, dry ether CH3 - CH = C - CH 2 - CH3
(a) A – (r), B – (p), C – (s), D – (q) |
(b) A – (p), B – (s), C – (r), D – (q) CH 2 - CH 2 - CH3
(c) A – (s), B – (q), C – (p), D – (r) (a) 3–Ethyl–2–hexene (b) 3–Propyl–2–hexene
(d) A – (q), B – (p), C – (s), D – (r) (c) 3–Propyl–3–hexene (d) 4–Ethyl–4–hexene
23. Match the columns 30. The name of ClCH 2 - C = C - CH 2 Cl according to
Column-I Column-II | |
Br Br
Cu/523K/100 atm
(A) CH4 + O2¾¾¾¾¾¾¾ (p) HCHO
® IUPAC nomenclature system is
Mo O (a) 2, 3- dibromo -1, 4- dichlorobutene-2
(B) CH4 + O2 ¾¾¾¾
2 3®
D
(q) (CH3)3COH
(b) 1, 4- dichloro-2, 3- dibromobutene-2
(CH COO) Mn (c) Dichlorodibromobutene
(C) C2H6 + O2 ¾¾¾¾¾¾¾
3
D
2 ® (r) CH3OH
(d) Dichlorodibromobutane
KMnO 31. Which one of the following exhibits geometrical isomerism?
(D) (CH3)3CH ¾¾ ¾ ¾® 4
oxidation
(s) CH3COOH
(a) 1, 2-dibromopropene (b) 2, 3-dimethylbut-2-ene
(a) A – (s), B – (p), C – (r), D – (s)
(c) 2, 3-dibromobut-2-ene (d) Both (a) and (c)
(b) A – (q), B – (p), C – (s), D – (r)
32. The compounds CH3CH == CHCH3 and
(c) A – (r), B – (p), C – (s), D – (q)
CH3CH2CH == CH2
(d) A – (p), B – (q), C – (r), D – (s)
(a) are tautomers
24. Assertion : CH4 does not react with Cl2 in dark.
(b) are position isomers
Reason : Chlorination of CH4 takes place in sunlight.
(a) Assertion is correct, reason is correct; reason is a (c) contain same number of sp3 – sp3, sp3 – sp2 and sp2
correct explanation for assertion. – sp2 carbon-carbon bonds
(b) Assertion is correct, reason is correct; reason is not a (d) exist together in dynamic equilibrium
correct explanation for assertion 33. Consider the following statements : A hydrocarbon of
(c) Assertion is correct, reason is incorrect molecular formula C5H10 is a
(d) Assertion is incorrect, reason is correct. I. monosubstituted alkene
25. Assertion : Iodination of alkanes is reversible. II. disubstituted alkene
Reason : Iodination is carried out in presence of iodic acid. III. trisubstituted alkene
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Which of the following statement(s) is(are) correct?

Br
(a) I, II and III (b) I and II |
(c) II and III (d) I and III (b) CH3 - C- CH 2 - CH3
34. Geometrical isomerism is not shown by |
CH3
CH3
| (c) CH3 - CH- CH - CH 3
(a) CH3CH 2C= C CH 2CH 3 | |
| Br CH3
CH3
(d) CH 3 - CH - CH - CH 3
| |
(b) C 2 H 5 - C = C - CH 2 I
| | CH 3 Br
H H 43. Butene-1 may be converted to butane by reaction with
(c) CH 2 = C(Cl)CH3 (a) Sn – HCl (b) Zn – Hg
(c) Pd/H2 (d) Zn – HCl
(d) CH 3 - CH = CH - CH = CH 2 44. Alkenes usually show which type of reactions?
35. By which reaction ethene is obtained from ethyne? (a) addition (b) substitution
(a) oxidation (b) polymerisation (c) elimination (d) superposition
(c) hydrogenation (d) dehydrogenation 45. A reagent used to test unsaturation in alkene is -
36. The major product formed when 2-bromobutane is treated (a) ammonical Cu2Cl2 (b) ammonical AgNO3
with alcoholic KOH is (c) solution of Br2 in CCl4 (d) conc. H2SO4
(a) 2-Butanol (b) 1-Butene 46. In the given reaction
(c) 1-Butanol (d) trans-2-butene X
CH 3CH 2 CH = CHCH 3 ¾¾®
37. Ethyl alcohol is heated with conc. H 2SO4 . The product
CH3CH 2COOH +CH3COOH
formed is :
The X is
(a) H3C - C - OC2 H5 (b) C2 H 6
(a) C2 H5ONa (b) Conc. HCl +Anhy.ZnCl2
||
O (c) Anh. AlCl3 (d) KMnO4/OH–
47. The negative part of an addendum adds on to the carbon
(c) C2 H 4 (d) C2 H 2 atom joined to the least number of hydrogen atoms. This
38. When hydrochloric acid gas is treated with propene in statement is called
presence of benzoyl peroxide, it gives (a) Thiele’s theory (b) Peroxide effect
(a) 2-Chloropropane (b) Allyl chloride (c) Markownikoff’s rule (d) Baeyer’s strain theory
(c) No reaction (d) n-Propyl chloride. 48. In the following sequence of reactions, the alkene affords
39. "The addition of unsymmetrical reagents to unsymmetrical the compound ‘B’
alkenes occurs in such a way that the negative part of the O H O
CH 3 - CH = CH - CH 3 ¾¾3¾
® A ¾¾¾
2 ® B.
addendum goes to that carbon atom of the double bond Zn
which carries lesser number of hydrogen atoms" is called The compound B is
by : (a) CH3CH2CHO (b) CH3COCH3
(a) Saytzeff rule (b) Markownikoff's rule (c) CH3CH2COCH3 (d) CH3CHO
(c) Kharasch effect (d) Anti-Saytzeff rule 49. One mole of a symmetrical alkene on ozonolysis gives two
40. When one mole of an alkene on ozonolysis produces 2 moles moles of an aldehyde having a molecular mass of 44 u. The
of propanone, the alkene is alkene is
(a) 3-methyl-1-butene (b) 2, 3-dimethyl-1-butene (a) propene (b) 1-butene
(c) 2, 3-dimethyl-2-pentene (d) 2, 3-dimethyl-2-butene (c) 2-butene (d) ethene
41. Reaction of HBr with propene in the presence of peroxide 50. The alkene that will give the same product with HBr in the
gives absence as well as in the presence of peroxide is
(a) isopropyl bromide (b) 3-bromo propane (a) 2-butene (b) 1-butene
(c) allyl bromide (d) n-propyl bromide (c) propene (d) 1-hexene

42. H 3 C - CH - CH = CH 2 + HBr ® A 51. Ethylene reacts with alkaline KMnO4 to form

|
(a) Oxalic acid (b) HCHO
CH 3 (c) Ethyl alcohol (d) Glycol
A(predominantly) is : 52. The reaction of HI with CH3 – CH = CH2 at 400°C yields :
(a) CH 3 - CH - CH 2 - CH 2 Br (a) CH2 I – CH = CH2 (b) CH3 – CHI – CH3
|
(c) CH3 – CH2 – CH2 I (d) CH2I – CH2 – CH2I
CH 3
HYDROCARBONS 171

53. Ethene when treated with Br2 in the presence of CCl4 which (b) Assertion is correct, reason is correct; reason is not a
compound is formed? correct explanation for assertion
(a) 1, 2-dibromoethane (b) 1-bromo-2-chloroethane (c) Assertion is correct, reason is incorrect
(c) Both (a) and (b) (d) 1, 1, 1-tribromoethane (d) Assertion is incorrect, reason is correct.
54. The test for unsaturation is confirmed by the decolourisation 61. The nodal plane in the p-bond of ethene is located in
of which of the following (a) the molecular plane
(a) Iodine water (b) CuSO4 solution (b) a plane parallel to the molecular plane
(c) Bromine water (d) All of these (c) a plane perpendicular to the molecular plane which bisects
55. Isopropyl alcohol is obtained by reacting which of the the carbon - carbon s -bond at right angle
following alkenes with conc. H2SO4 and H2O (d) a plane perpendicular to the molecular plane which
(a) Ethylene (b) Propylene contains the carbon - carbon s -bond.
(c) 2-methyl propene (d) Isoprene 62. The IUPAC name of the compound having the formula
56. Which of the following statements are correct ? (CH3)3CCH = CH2 is –
(i) The general formula of alkenes is CnH2n. (a) 3, 3, 3-trimethyl-1-propane
(ii) Alkenes are also known as paraffins. (b) 1, 1, 1-trimethyl-1-butene
(iii) Bond length of C–C double bond in alkene is shorter (c) 3, 3-dimethyl-1-butene
than C–C single bond in alkane. (d) 1, 1-dimethyl-1, 3-butene
(iv) Carbon–Carbon double bond in alkene consists of two 63. Correct order of stability is :
sigma bonds. (a) cis -2- butene > 1-butene > trans -2-butene
(v) Alkenes are easily attacked by electrophilic reagent. (b) trans-2-butene > cis-2-butene > 1-butene
(a) (i) and (iv) (b) (i), (iii) and (v) (c) 1-butene > cis-2-butene > trans-2- butene
(c) (i) and (iii) (d) (i), (ii), (iv) and (v) (d) cis-2-butene > trans-2-butene > 1-butene
57. Which of the following statements are correct ? 64. Which of the following is correct set of physical properties
(i) Cis form of alkene is polar whereas trans form is of the geometrical isomers?
non-polar CH3 CH3
(ii) Cis form of alkene is non-polar whereas trans form is
polar.
(iii) In case of solid alkenes the trans isomer has higher
melting point than the cis isomer. Dipole moment B.P. M.P. Stability
(iv) Cis and trans both form have same properties. (a) I > II I > II II > I I > II
(a) (i) and (iii) (b) (ii) and (iii) (b) II > I II > I II > I II > I
(c) (i), (iii) and (iv) (d) (i) and (iv) (c) I > II I > II I > II I > II
58. Match the columns (d) II > I II > I I > II I > II
Column-I Column-II 65. But-2-ene exhibits cis,trans-isomerism due to
(A) CH º CH + H2 ¾¾ ® CH 2 = CH 2 (p) Zn (a) rotation around C3 – C4 sigma bond
(B) CH 3CH 2 Br ¾¾
® CH2 = CH2 (q) Conc. H2SO4 (b) restricted rotation around C = C bond
(c) rotation around C1 – C2 bond
(C) CH 2 BrCH 2 Br ¾¾ ® CH2 = CH2 (r) Pd/C (d) rotation around C2 – C3 double bond
(D) CH3CH2OH ¾¾ ® CH2 = CH2 (s) Alc. KOH 66. When 3, 3-dimethyl 2-butanol is heated with H2SO4, the
(a) A – (r), B – (s), C – (p), D – (q) major product obtained is
(b) A – (s), B – (r), C – (q), D – (p) (a) 2,3-dimethyl 2-butene
(c) A – (q), B – (p), C – (s), D – (r) (b) 3, 3-dimethyl 1- butene
(d) A – (r), B – (s), C – (q), D – (p) (c) 2, 3-dimethyl 1- butene
59. Assertion : 1-Butene on reaction with HBr in the presence (d) cis & trans isomers of 2, 3-dimethyl 2-butene
of a peroxide produces 1-bromobutane. 67. Reaction of hydrogen bromide with propene in the absence
Reason : It involves the free radical mechanism. of peroxide is a/an
(a) Assertion is correct, reason is correct; reason is a (a) free radical addition
correct explanation for assertion. (b) nucleophilic addition
(b) Assertion is correct, reason is correct; reason is not a (c) electrophilic substitution
correct explanation for assertion (d) electrophilic addition
(c) Assertion is correct, reason is incorrect 68. CH2 = CHCl reacts with HCl to form
(d) Assertion is incorrect, reason is correct. (a) CH2Cl – CH2Cl (b) CH3 – CHCl2
60. Assertion : All the hydrogen atoms in CH2 = C = CH2 lie in (c) CH2 = CHCl.HCl (d) None of these
one plane. 69. The only alcohol that can be prepared by the indirect
Reason : Carbon atoms are sp2 and sp hybridized. hydration of alkene is
(a) Assertion is correct, reason is correct; reason is a (a) Ethyl alcohol (b) Propyl alcohol
correct explanation for assertion. (c) Isobutyl alcohol (d) Methyl alcohol
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70. In the presence of peroxide, hydrogen chloride and hydrogen (a) CH 3CH 2 CH 2 C º CCH 2CH 2 CH3
iodide do not give anti-Markownikov’s addition to alkenes
because (b) CH 3CH 2C º CH
(a) Both are highly ionic (c) CH 3CH = CHCH3
(b) One is oxidising and the other is reducing
(c) One of the steps is endothermic in both the cases (d) CH 3CH 2C º CCH 2CH3
(d) All the steps are exothermic in both the cases 81. Which of these will not react with acetylene?
71. Which of the following statements is incorrect regarding (a) NaOH (b) Ammonical AgNO3
dehydrohalogenation of alkenes ? (c) Na (d) HCl.
(a) During the reaction hydrogen atom is eliminated from 82. When acetylene is passed over heated iron tube, the product
the b - carbon atom. obtained is –
(b) Rate of reaction for same alkyl group; (a) C2H2 (b) C4H4 (c) C6H6 (d) C8H8
Iodine > Bromine > Chlorine 83. But–2–yne on chlorination gives
(c) Rate of reaction; (CH3)3C – > (CH3)2CH – > CH3CH2 – (a) 1 –chlorobutane
(d) Only nature of halogen atom determines rate of the (b) 1, 2 –dichlorobutane
reaction. (c) 1, 1, 2, 2 –tetrachlorobutane
(d) 2, 2, 3, 3 –tetrachlorobutane
Topic 3: Alkynes
84. When propyne reacts with aqueous H2SO4 in the presence
72. The IUPAC name of the compound of HgSO4, the major product is
CH3CH = CHC º CH is (a) Propanal
(a) Pent-l-yn-3-ene (b) Pent-4-yn-2-ene (b) Propyl hydrogen sulphate
(c) Pent-3-en-1-yne (d) Pent-2-en-4-yne (c) Acetone
73. Number of alkynes for formula C5H8 is – (d) Propanol
(a) 2 (b) 3 (c) 4 (d) 5 85. Propyne on polymerisation gives
(a) Mesitylene (b) Benzene
Reagent
74. R - CH 2 - CCl 2 - R ¾¾¾¾® R - C º C - R (c) Ethyl benzene (d) Propyl benzene
The reagent is 86. What happens when a mixture of acetylene and hydrogen
(a) Na (b) HCl in H2O is passed over heated Lindlar’s catalyst ?
(c) KOH in C2H5OH (d) Zn in alcohol. (a) Ethane and water are formed
75. Calcium carbide when treated with water gives : (b) Ethylene is formed
(a) ethylene (b) methane (c) Acetylene and ethane are formed
(c) acetylene (d) ethane (d) None of these
76. Which one of the following has the minimum boiling 87. Which of the following reaction is shown by alkynes ?
point ? (a) Addition (b) Substitution
(a) 1-Butene (b) 1-Butyne (c) Polymerization (d) All of these
(c) n- Butane (d) Isobutane 88. Which of the following reactions will yield 2,
77. Ammonical silver nitrate forms a white precipitate easily 2-dibromopropane ?
with (a) HC º CH + 2HBr ®
(a) CH3C º CH (b) CH3C º CCH3 (b) CH3C º CH + 2HBr ®
(c) CH3CH = CH 2 (d) CH2 = CH2 (c) CH3CH = CH 2 + HBr ®
78. When acetylene is passed through dil. H2SO4 in presence (d) CH3CH = CHBr + HBr ®
of HgSO4, the compound formed is
(a) ether (b) acetaldehyde 89. In the given reactions
A
(c) acetic acid (d) ketone CH 3C º CH ¾¾® CH 3CBr2 CHBr2
79. Which of the following will be the final product when C 2H2 B
reacts with HCl CH 3C º CH ¾¾
® CH 3CBr2 CH 3
Hg 2 + H +
CH 2 CH3 CH3C º CH ¾¾¾¾¾
®C
333 K
(a) P (b) |
CHCl CHCl 2 Hg 2+ H +
HC º CH ¾¾¾¾¾
®D
333 K
CHCl A, B, C and D are respectively
(c) P (d) None of these (a) HBr, Br2, CH3COCH3, CH3CHO
CHCl
(b) Br2, HBr, CH3COCH3, CH3CHO
80. The hydrocarbon which can react with sodium in liquid (c) HBr, HBr, CH3COCH3, CH3CHO
ammonia is (d) Br2, HBr, CH3CH2CHO, CH3CHO
 HYDROCARBONS 173

90. Which of the following polymer can be used as electrodes Topic 4: Aromatic Hydrocarbons
in batteries ?
98. Aromatic compounds burn with sooty flame because
(a) Polypropene (b) Polyacetylene
(a) they have a ring structure of carbon atoms
(c) Polyethene (d) Polyisoprene
(b) they have a relatively high percentage of hydrogen
91. Which of the following statements are correct ?
(c) they have a relatively high percentage of carbon
(i) Alkynes on reduction with palladised charcoal form
(d) they resist reaction with oxygen of air
cis alkenes.
99. The conditions for aromaticity is :
(ii) Alkynes on reduction with palladised charcoal form
(a) molecule must have cyclic clouds of delocalised p
trans alkenes.
electrons
(iii) Alkynes on reduction with sodium in liquid ammonia
(b) molecule must contain (4n + 2) p electrons
form trans alkenes.
(c) Both (a) and (b)
(iv) Propyne on reduction with palladised charcoal form a
(d) None of the above
mixture of cis and trans propene.
100. Select the true statement about benzene amongst the
(a) (i) and (iv) (b) (i) and (iii)
following
(c) (ii) and (iv) (d) (i), (iii) and (iv)
(a) Because of unsaturation benzene easily undergoes
92. How many structural isomers are possible for the alkyne
addition
C6H10 ?
(b) There are two types of C – C bonds in benzene molecule
(a) 7 (b) 6 (c) 8 (d) 5
(c) There is cyclic delocalisation of pi-electrons in benzene
93. Which of the following will have least hindered rotation
(d) Monosubstitution of benzene gives three isomeric
around carbon - carbon bond ?
products.
(a) Ethane (b) Ethylene
101. Benzene can be directly obtained from
(c) Acetylene (d) Hexachloroethane
(a) Acetylene (b) Phenol
94. Acetylenic hydrogens are acidic because
(c) Chlorobenzene (d) All the above
(a) Sigma electron density of C – H bond in acetylene is
nearer to carbon, which has 50% s-character COONa
(b) Acetylene has only one hydrogen on each carbon
(c) Acetylene contains least number of hydrogens among 102. NaOH + CaO
A
the possible hydrocarbons having two carbons
(d) Acetylene belongs to the class of alkynes with
molecular formula, CnH2n – 2. The product A is
95. The correct increasing order of acidity of the following (a) Benzene (b) Benzaldehyde
alkynes (c) Toluene (d) Benzoic acid
103. In a reaction of C6H5Y, the major product (> 60%) is
(1) CH3 - C º C - CH3
m-isomer, so the group Y is
(2) CH3 - C º CH (a) –COOH (b) –NH2
(3) CH º CH (c) –OH (d) –Cl
(a) 1 < 2 < 3 (b) 2 < 3 < 1 HNO Br
(c) 3 < 2 < 1 (d) 1 < 3 < 2 104. ¾¾¾¾ 3 ® A ¾¾¾®2 B. The compound B is
H SO 2 FeBr
4 2
96. Identify the alkyne in the following sequence of reactions.
H Ozonolysis Wacker NO2 NO2
Alkyne ¾¾¾¾¾¾¾
2 ® A ¾¾¾¾¾
® B ¬¾¾¾¾
Lindlar's catalyst only Process Br
(a) (b)
(a) H3C - C º C - CH3
Br
(b) H3C - CH 2 - C º CH NO2
NO2
=
(c) H 2C CH - C º CH
(d) HC º C - CH 2 - C º CH (c) (d)
97. Which of the following represents the correct order of acidic Br Br
Br
strength ?
105. Chlorobenzene is o, p-directing in electrophilic substitution
(i) HC º CH > H 2C = CH 2 > CH3 - CH3
reaction. The directing influence is explained by
(ii) HC º CH > CH3 - CH3 > H 2C = CH 2 (a) + M of Ph (b) +I of Cl
(iii) CH3C º CH > HC º CH > CH3 - C º C - CH3 (c) + M of Cl (d) + I of Ph
(iv) HC º CH > CH3 - C º CH > CH3 - C º C - CH3 106. Catalytic hydrogenation of benzene gives
(a) (i) and (iii) (b) (ii) and (iv) (a) xylene (b) cyclohexane
(c) (i) and (iv) (d) (i) and (iv) (c) benzoic acid (d) toluene
 EBD_7374
174 CHEMISTRY

107. The strongest ortho - para and strongest meta - directing (iv) They are also produced in human body due to various
groups respectively are biochemical reactions.
(a) –NO2 and –NH2 (b) –CONH2 and –NH2 (a) (i), (ii) and (iv) (b) (i), (iii) and (iv)
(c) –NH2 and –CONH2 (d) –NH2 and –NO2 (c) (ii), (iii) and (iv) (d) (i), (ii) and (iii)
108. For the formation of toluene by Friedal Craft reaction, 118. Match the following reactants in Column I with the
reactants used in presence of anhydrous AlCl 3 are corresponding reaction products in Column II and choose
(a) C2H2 and CCl4 (b) CH4 and CaCN2 the correct option from the codes given below.
(c) C6H6 and CH3Cl (d) C2H5 OH and Zn Column - I Column - II
109. Benzene can be obtained in the reaction AlCl3
(A) Benzene + Cl2 ¾¾¾® (p) Benzoic acid
(a) Ethene + 1, 3-butadiene
(b) Trimerisation of ethyne (B) Benzene + CH3Cl (q) Methyl phenyl
(c) Reduction of PhCHO AlCl3
¾¾¾® ketone
(d) All of these
(C) Benzene + CH3COCl (r) Toluene
BHC, anhydrous
110. C6 H6 + CH3Cl ¾¾¾¾¾¾¾ ® C6 H5CH3 + HCl AlCl
AlCl 3 ¾¾¾®
3
is an example of
KMnO4 / NaOH
(a) Friedel - Craft’s reaction (D) Toluene ¾¾¾¾¾¾ ¾
® (s) Chlorobenzene
(b) Kolbe’s synthesis (a) A – (s), B – (r), C – (q), D – (p)
(c) Wurtz reaction (b) A – (s), B – (r), C – (p), D – (q)
(d) Grignard reaction (c) A – (r), B – (s), C – (p), D – (q)
111. Benzene reacts with CH3COCl + AlCl3 to give (d) A – (r), B – (s), C – (q), D – (p)
(a) chlorobenzene (b) toluene 119. Match the columns
(c) benzyl chloride (d) acetophenone Column - I Column - II
112. Benzene on reaction with ozone forms __________. (A) Alkyl halide + Alkyl halide (p) Sulphonation
(a) 2 molecules of aldehyde and 1 molecule of ketone in presence of dry ether
(b) 2 molecules of ketone and 1 molecule of aldehyde (B) Arene + Acid halide (q) Wurtz reaction
(c) triozonide in presence of AlCl3
(d) hexaozonide (C) Arene + Fuming sulphuric (r) Catalytic
113. AlCl3 acts as ________ in Friedel-Crafts reaction in presence of AlCl3 hydrogenation
(a) nucleophile (b) electrophile (D) Arene + Hydrogen (s) Friedel-Crafts
(c) free radical (d) intermediate in presence of Ni reaction
114. The electrophilic substitution reactions of benzene takes (a) A - (p), B - (r), C - (q); D - (s)
place via (b) A - (s), B - (q), C - (r); D - (p)
(i) generation of electrophile (c) A - (r), B - (p), C - (s); D - (q)
(ii) generation of nucleophile (d) A - (q), B - (s), C - (p); D - (r)
(iii) formation of carbocation intermediate 120. Match the columns
(iv) removal of proton from the carbocation intermediate Column - I Column - II
(a) (i), (iii) and (iv) (b) (ii), (iii) and (iv) (A) Aromatic (p) Planar
(c) (i) and (iv) (d) (ii) and (iv) (B) Antiaromatic (q) Non-planar
115. During the nitration of benzene. In the process of generation (C) Huckel rule (r) 4 np localised
of nitronium ion sulphuric acid behaves as a/an ______ electrons
and nitric acid behave as a/an _________. (D) Cyclo-octatetraene (s) (4 n + 2)p delocalised
(a) base, acid (b) acid, base electrons
(c) strong acid, weak acid (d) weak acid, strong acid (a) A - (p, s), B - (p, r), C - (s), D - (q, r)
116. Benzene is highly unsaturated but it does not undergo (b) A - (p, r), B - (p, s), C - (s), D - (q, r)
addition reaction because (c) A - (p, s), B - (s), C - (p, r), D - (q, r)
(a) p-electrons of benzene are delocalised. (d) A - (q, r), B - (p, r), C - (s), D - (p, s)
(b) cyclic structures do not show addition reaction 121. Assertion : Tropylium cation is aromatic in nature
(c) benzene is a non-reactive compound
(d) All of the above
117. Which of the following statements are correct ?
(i) Polynuclear hydrocarbons contain two or more benzene Reason : The only property that determines its aromatic
rings fused together. behaviour is its planar structure.
(ii) Polynuclear hydrocarbons have carcinogenic property. (a) Assertion is correct, reason is correct; reason is a
(iii) Polynuclear hydrocarbons are formed on incomplete correct explanation for assertion.
combustion of organic materials like tobacco, coal and (b) Assertion is correct, reason is correct; reason is not a
petroleum. correct explanation for assertion
HYDROCARBONS 175

(c) Assertion is correct, reason is incorrect (b) 7 p-orbitals and 7 unpaired electrons
(d) Assertion is incorrect, reason is correct. (c) 6 p-orbitals and 7 unpaired electrons
122. Which one of these is not compatible with arenes? (d) 6 p-orbitals and 6 unpaired electrons
(a) Greater stability 127. (i) Chlorobenzene and (ii) benzene hexachloride are
obtained from benzene by the reaction of chlorine, in the
(b) Delocalisation of p-electrons
pesence of
(c) Electrophilic additions
(a) (i) Direct sunlight and (ii) anhydrous AlCl3
(d) Resonance (b) (i) Sodium hydroxide and (ii) sulphuric acid
123. The carbon-carbon bond length in benzene is (c) (i) Ultraviolet light and (ii) anhydrous FeCl3
(a) Same as in C2H4 (d) (i) Anhydrous AlCl3 and (ii) direct sunlight
(b) In between C2H6 and C2H2 128. A group which deactivates the benzene ring towards
(c) In between C2H4 and C2H2 electrophilic substitution but which directs the incoming
(d) In between C2H6 and C2H4 group principally to the o-and p-positions is
124. Point out the wrong statement in relation to the structure of (a) –NH2 (b) –Cl (c) –NO2 (d) –C2H5
benzene 129. Benzene can be obtained by heating either benzoic acid
with X or phenol with Y. X and Y are respectively.
(a) It forms only one monosubstitution product
(a) Zinc dust and soda lime
(b) The C - C bond distance in benzene is uniformly 1.397Å (b) Soda lime and zinc dust
(c) It is a resonance hybrid of a number of canonical forms (c) Zinc dust and sodium hydroxide
(d) It has three delocalised p-molecular orbitals (d) Soda lime and copper
125. The ratio of s to p bonds in benzene is : 130. Which of the following chemical system is non aromatic?
(a) 2 (b) 3 (c) 4 (d) 8
(a) (b)
.
126. The radical, CH2 is aromatic because it has :

(a) 7 p-orbitals and 6 unpaired electrons (c) (d)

S

Exercise 2 : Exemplar & Past Year MCQs

NCERT Exemplar MCQs (c) 3-ethyl-5-isopropyloctane
(d) 3-isopropyl-6-ethyloctane
1. Arrange the following in decreasing order of their boiling 5. The addition of HBr to 1-butene gives a mixture of products
points. A, B and C.
1. n–butane 2. 2-methylbutane
3. n–pentane 4. 2, 2-dimethylpropane Br C2H5
(a) 1 > 2 > 3 > 4 (b) 2 > 3 > 4 > 1
(c) 4 > 3 > 2 > 1 (d) 3 > 2 > 4 > 1 C C
(A) H5C2 CH3 (B) H CH3
2. Arrange the halogens F2, Cl2, Br 2, I2, in order of their
increasing reactivity with alkanes. H Br
(a) I2 < Br2 < Cl2 < F2 (b) Br2 < Cl2 < F2 < I2 (C) CH3 - CH 2 - CH 2 - CH 2 - Br
(c) F2 < Cl2 < Br2 < I2 (d) Br2 < I2 < Cl2 < F2
The mixture consists of
3. The increasing order of reduction of alkyl halides with zinc
(a) A and B as major and C as minor products
and dilute HCl is
(b) B as major, A and C as minor products
(a) R – Cl < R – I < R – Br (b) R — Cl < R – Br < R – I
(c) B as minor, A and C as major products
(c) R – I < R – Br < R – Cl (d) R – Br < R – I < R – Cl
(d) A and B as minor and C as major products
4. The correct IUPAC name of the following alkane is
6. Which of the following will not show geometrical isomerism?
H3 C - CH2 - CH - CH2 - CH2 - CH - CH2 - CH3 F H F F
| | (a) C=C (b) C=C
CH CH 2 Cl D Cl Cl
|
CH3 H3C C2H5 CH3 CH3
CH3 CH3
(c) C=C (d) C=C
(a) 3, 6-diethyl-2-methyloctane H5C2 CH3 C2H5
CH3
(b) 5-isopropyl-3-ethyloctane
 EBD_7374
176 CHEMISTRY

7. Arrange the following hydrogen halides in order of their 14. Assertion : Tropylium cation is aromatic in nature
decreasing reactivity with propene.
(a) HCl > HBr > HI (b) HBr > HI > HCl
(c) HI > HBr > HCl (d) HCl > HI > HBr
8. Arrange the following carbanions in order of their decreasing Reason : The only property that determines its aromatic
stability. behaviour is its planar structure. [AIIMS 2014, 2016, C]
A. H3C — C º C – B. H — C º C – (a) If both Assertion and Reason are correct and Reason
C. H3C — CH 2 is the correct explanation of Assertion.
(b) If both Assertion and Reason are correct, but Reason
(a) A > B > C (b) B > A > C
is not the correct explanation of Assertion.
(c) C > B > A (d) C > A > B
(c) If Assertion is correct but Reason is incorrect.
9. Arrange the following alkyl halides in decreasing order of
(d) If both the Assertion and Reason are incorrect.
the rate of b – elimination reaction with alcoholic KOH.
15. The major organic compound formed by the raction of
H 1, 1, 1-trichloroethane with silver powder is:
| [JEE M 2014, S]
A. CH3 - C - CH 2 Br (a) Acetylene (b) Ethene
|
(c) 2 - Butyne (d) 2 - Butene
CH3
16. An organic compound A (C4H9Cl) on reaction with Na/
B. CH3 — CH2 — Br diethyl ether gives a hydrocarbon which on
C. CH3 — CH2 — CH2 — Br monochlorination gives only one chloro derivative, then A
(a) A > B > C (b) C > B > A is [BITSAT 2014, C]
(c) B > C > A (d) A > C > B (a) tert-butyl chloride (b) sec-butyl chloride
10. Which of the following reactions of methane is incomplete (c) isobutyl chloride (d) n-butyl chloride
combustion? 17. 2,3-Dimethyl-2-butene can be prepared by heating which of
Cu / 523 K /100 atm the following compounds with a strong acid ?
(a) 2CH 4 + O 2 ¾¾¾¾¾¾¾¾
® 2CH 3OH [AIPMT 2015 RS, S]
Mo O
(b) CH 4 + O 2 ¾¾¾¾
2 3 ® HCHO + H O
2 (a) (CH3)2 CH – CH – CH = CH2
|
CH3
(c) ® C ( s ) + 2H 2 O ( l )
CH 4 + O 2 ¾¾
(b) (CH3)3 C – CH = CH2
(d) ® CO 2 ( g ) + 2H 2 O ( l )
CH 4 + 2O 2 ¾¾ (c) (CH3)2C = CH – CH2 – CH3
Past Year MCQs (d) (CH3)2CH – CH2 – CH = CH2
11. Which of the following organic compounds has same 18. In the reaction with HCl, an alkene reacts in accordance
hybridization as its combustion product (CO2)? with the Markovnikoff's rule, to give a product 1-chloro-1-
[AIPMT 2014, S] methylcyclohexane. The possible alkene is :
(a) Ethane (b) Ethyne [AIPMT 2015 RS, A]
(c) Ethene (d) Ethanol CH2 CH3
12. Predict the nature of P in the following reaction
NaNH / inert solvent
2 ¾ ¾ ¾¾® P (a) (b)
CH 3 C º CCH 3 ¾¾ ¾ ¾
heat

(a) CH2 = CHCH = CH2 [AIIMS 2014, C]

(b) CH2= C = CH – CH3 CH3
(c) CH3CH2C º CH
(c) (a) and (b) (d)
(d) No reaction
13. Assertion : Trans-2-butene on reaction with Br2 gives meso-
2, 3-dibromobutane. [AIIMS 2009, 2014, C] 19. A single compound of the structure : [AIPMT 2015, A]
Reason : The reaction involves syn-addition of bromine. CH3 CH3
(a) If both Assertion and Reason are correct and Reason OHC C C
is the correct explanation of Assertion. C H C O
(b) If both Assertion and Reason are correct, but Reason H2 H2
is not the correct explanation of Assertion. is obtainable from ozonolysis of which of the following cyclic
(c) If Assertion is correct but Reason is incorrect. compounds ?
(d) If both the Assertion and Reason are incorrect.
HYDROCARBONS 177

(a) Bromine in carbon tetrachloride

H3C H3C CH3 (b) Bromine in acetic acid
(a) (b) (c) Alk KMnO4
H3C
(d) Ammonical silver nitrate.
25. Assertion : 1-Butene on reaction with HBr in the presence of a
CH3 peroxide produces 1-bromobutane. [AIIMS 2015, C]
H3C Reason : It involves the formation of a primary radical.
(c) (d) CH3 (a) If both Assertion and Reason are correct and Reason
CH3 is the correct explanation of Assertion.
(b) If both Assertion and Reason are correct, but Reason
20. The total number of p-bond electrons in the following is not the correct explanation of Assertion.
structure is : [AIPMT 2015, S] (c) If Assertion is correct but Reason is incorrect.
H H H (d) If both the Assertion and Reason are incorrect.
H3C 26. Which compound would give 5 - keto - 2 - methylhexanal
CH3 upon ozonolysis ? [JEE M 2015, A]
H3C CH3
CH3
H2C H CH3
(a) (b) H3C
(a) 8 (b) 12 (c) 16 (d) 4
21. Given: CH3
CH3
H3C CH3 H3C CH2 H2C CH2 CH3

(c) CH3 (d)

CH3
CH3 CH3 CH2 27. In the reaction
(I) (II) (III) (i) NaNH 2 / liq.NH3 (i) NaNH 2 / liq.NH 3
H - C º CH X Y
(ii) CH3CH 2 Br (ii) CH 3 CH 2 Br
The enthalpy of the hydrogenation of these compounds
will be in the order as : [AIPMT 2015, C] X and Y are [NEET 2016, S]
(a) III > II > I (b) II > III > I (a) X = 1-Butyne ; Y = 3-Hexyne
(c) II > I > III (d) I > II > III (b) X = 2-Butyne ; Y = 3-Hexyne
22. The oxidation of benzene by V2O5 in presence of air (c) X = 2-Butyne ; Y = 2-Hexyne
produces : [AIPMT 2015 RS, C] (d) X = 1-Butyne ; Y = 2-Hexyne
(a) benzoic anhydride (b) maleic anhydride 28. The alkene that will give the same product with HBr in the
(c) benzoic acid (d) benzaldehyde absence as well as in the presence of peroxide is
23. The reaction of C6H5CH = CHCH3 with HBr produces: [AIIMS 2016, S]
[AIPMT 2015, A] (a) 2-butene (b) 1-butene
(a) C6 H5CH 2CHCH3 (b) C6 H5CH 2CH 2CH 2Br (c) propene (d) 1-hexene
| 29. Assertion : Energy of resonance hybrid is equal to the
Br average of energies of all canonical forms.
CH=CHCH3
Reason : Resonance hybrid cannot be presented by a single
structure. [AIIMS 2016, C]
(c) (d) C 6 H 5 C HCH 2 CH3 (a) If both Assertion and Reason are correct and Reason
| is the correct explanation of Assertion.
Br
(b) If both Assertion and Reason are correct, but Reason
Br is not the correct explanation of Assertion.
24. Which is the most suitable reagent among the following to (c) If Assertion is correct but Reason is incorrect.
distinguish compound (3) from rest of the compounds ? (d) If both the Assertion and Reason are incorrect.
[AIIMS 2015, S] 30. The reaction of propene with HOCl (Cl 2 + H2O) proceeds
1. CH3– C º C – CH3 through the intermediate: [JEE M 2016, C]
2. CH 3 - CH 2 - CH 2 - CH 3 (a) CH 3 – CH ( OH ) - CH 2+
3. CH 3 - CH 2C º CH (b) CH 3 – CHCl - CH 2+
4. CH 3 - CH = CH 2.
(c) CH 3 – CH + - CH 2 – OH
(d) CH 3 – CH + - CH 2 – Cl
 EBD_7374
178 CHEMISTRY

31. The product of the reaction given below is: (a) A : H3C – C = CH2 B : H3C – C = CH2
| |
1. NBS/hv OH SO4
2. H 2O/K 2CO 3
X
[JEE M 2016, S] (b) A : H3C - C - CH3 B : H3C – C º CH
||
O
O CO2H
(c) A : H3C – C = CH2 B : H3C – C – CH3
| ||
(a) (b) OH O
(d) A : H3C – C = CH2 B : H3C - C - CH3
| ||
OH O
SO4
(c) (d) 37. The end product (C) in the following sequence of reactions is
[AIIMS 2017, A]
32. Give the possible structure of X in the following reaction : 1% HgSO
HC º CH ¾¾ ¾ ¾¾
4 ® A ¾¾ ¾
3 ¾
¾® B ¾¾®
CH MgX
¾ (C )
[O]
[BITSAT 2016, A] 20% H 2SO 4 H 2O
D O (a) acetic acid (b) isopropyl alcohol
C6H6 + D2SO4 ¾¾¾
2 ®
X
(c) acetone (d) ethanol
SO3D SO3D
38. In the given reaction
D X
(a) (b) CH3CH 2 CH = CHCH3 ¾¾®
CH3CH 2COOH +CH3COOH
The X is [AIIMS 2017, A]
D
SO3H (a) C2 H5ONa
D D
(b) Conc. HCl +Anhy.ZnCl2
D
(c) (d) (c) Anh. AlCl3
D D (d) KMnO4/OH–
D 39. Assertion : Benzene exhibit two different bond lengths, due
to C – C single and C = C double bonds. [AIIMS 2017, C]
H /Pt D /Pt
33. CH3C º CCH3 ¾¾¾¾ 2 ® A ¾¾¾¾ 2 ® B Reason : Actual structure of benzene is a hybrid of
The compounds A and B, respectively are following two structures.
[BITSAT 2016, A]
(a) cis-but-2ene and rac-2, 3-dideuterobutane ¬¾®
(b) trans-but-2ene and rac-2, 3-dideuterobutane
(c) cis-but-2ene and meso-2, 3-dideuterobutane 40. 3-Methyl-pent-2-ene on reaction with HBr in presence of
(d) trans-but-2ene and meso-2, 3-dideuterobutane peroxide forms an addition product. The number of possible
34. With respect to the conformers of ethane, which of the stereoisomers for the product is : [JEE M 2017, C]
following statements is true ? [NEET 2017, C]
(a) Six (b) Zero (c) Two (d) Four
(a) Bond angle changes but bond length remains same
(b) Both bond angle and bond length change 41. In the following structures, which two forms are staggered
(c) Both bond angles and bond length remains same conformations of ethane ? [BITSAT 2017, C]
(d) Bond angle remains same but bond length changes H
35. Which one is the correct order of acidity ? [NEET 2017, C] H H H
(a) CH º CH > CH3 – C º CH > CH2 = CH2 > CH3 – CH3 H
(b) CH º CH > CH2 = CH2 > CH3 – C º CH > CH3 – CH3 H
(c) CH3 – CH3 > CH2 = CH2 > CH3 – C º CH> CH º CH H H
H
(d) CH2 = CH2 > CH3 – CH = CH2 > CH3 – C º CH > CH º CH H
36. Predict the correct intermediate and product in the following H
reaction : [NEET 2017, S] H
H O, H SO (1) (2)
H3C - C º CH ¾¾¾¾¾¾
2 2 4 ® Intermediate ® product
HgSO 4 (A) (B)
HYDROCARBONS 179

H 45. What is impact on benzene in magnetic field?

H [AIIMS 2018, C]
H (a) Strongly attract (b) Weakly attract
H (c) Strongly repel (d) Weakly repel
H
H H 46. The trans-alkenes are formed by the reduction of alkynes
H H H H
H with: [JEE M 2018, C]
(3) (4) (a) H2-Pd/C, BaSO4 (b) NaBH4
(a) 1 and 4 (b) 2 and 3 (c) 1 and 2 (d) 1 and 3 (c) Na/liq. NH3 (d) Sn - HCl
42. Hydrocarbon (A) reacts with bromine by substitution to 47. In a set of reactions, ethylbenzene yielded a product D.
form an alkyl bromide which by Wurtz reaction is converted CH2CH 3 KMnO Br2 C 2H 5OH
to gaseous hydrocarbon containing less than four carbon ¾¾¾® 4
B ¾¾® C ¾¾¾®H+
D
KOH FeCl
atoms. (A) is [NEET 2018, S] 3

(a) CH º CH (b) CH2 = CH2 [BITSAT 2018, A]

(c) CH4 (d) CH3 – CH3
43. The compound C7H8 undergoes the following reactions: CH2 – CH – COOC 2H5
(a)
3Cl / D Br /Fe Zn /HCl Br
C7 H8 ¾¾¾¾
2 ® A ¾¾¾¾
2 ® B ¾¾¾¾® C
The product 'C' is [NEET 2018, S] Br
(a) m-bromotoluene
(b) o-bromotoluene (b)
(c) p-bromotoluene Br
(d) 3-bromo-2,4,6-trichlorotoluene
CH2 COOC2H5
44. In the reaction, Ph – CH2 – CH2 – C º C – CH3
Na/NH Cl2 /hv COOH
¾¾¾¾ 3® A
¾¾¾¾ ® B, B is [AIIMS 2018, A]
(a) Ph – CH(Cl) – CH2 CH3
C=C (c)
H H OCH2CH3
(b) Ph – CH(Cl) – CH2 H
C=C COOC2H5
H CH3
(c) Ph – CH2 – CH(Cl) – CH = CH – CH3 (d)
(d) None of these Br

Exercise 3 : Try If You Can

1. Arrange in the correct order of stability (decreasing order) (a) (I) > (II) > (III) > (IV) (b) (IV) > (III) > (II) » (I)
for the following molecules : (c) (I) > (II) » (III) > (IV) (d) (III) > (I) » (II) > (IV)
Me CH3 Ha
2.
Hb
H
H + Br• ®
(I) (II) H Me d
H OH
Me H
Me CH2 ¾ H c

H Br• will abstract which of the hydrogen most readily?

(a) a (b) b (c) c (d) d
H Me 3. An organic compound C4H6 on ozonolysis give HCHO, CO2,
H CH3CHO. Compound will be:
(III) (IV) H
(a) H2C CH — CH CH2
Me Me
Me (b) CH3— CH C CH2
 EBD_7374
180 CHEMISTRY

(c) CH3— C C — CH3 8. Products of the following reaction:

(d) (1) O
CH3CºCCH2CH3 ¾¾¾¾¾¾ 3
(2) oxidation
® ...... are:
CH3 CH3
C CH2 (a) CH3COOH + CO2
4. C CH2
CH3 CH3O (b) CH3COOH + HOOC ×CH2CH3
(A) (B) (c) CH3CHO + CH3CH2CHO
(d) CH3COOH + CH3COCH3
CH3
C CH2 9. Callene, C7H6, is expected to be a fairly polar aromatic
CH3OCH2 molecule. Which of the following resonance forms
contributes to the greatest extent towards the real structure
(C) (resonance hybrid) of the molecule?
Arrange the above in the decreasing order of reactivity
towards HBr:
(a) A > B > C (b) B > A > C + :–

(c) B > C > A (d) A > C > B (a) (b)

CH3
|
5. Isoprene, CH 2 = C - CH = CH 2 is treated with HCl, the
products formed will be a mixture of + –1

CH3 CH3
| | (c) (d)
(i) CH 3 - C - CH = CH 2 (ii) CH 2 = C - C = CH3 +
| |
Cl Cl
(P)
, hv
CH3 CH3 Cl 2
| |
(iii) CH 3 - C = CH - CH 2Cl (iv) ClCH 2 - C = CH - CH3 10. Cl
2 /A
lC
(a) (i) and (iii) (b) (ii) and (iii) l3

(c) (ii) and (iv) (d) All the four. (Q)

6. In the presence of platinum catalyst, hydrocarbon A adds Identify major product of both reactions P and Q respectively.
hydrogen to form n-hexane. When hydrogen bromide is
added to A instead of hydrogen, only a single bromo CH2 Cl
compound is formed. Which of the following is A?
Cl
(a) CH 3 — CH 2 — CH = CH — CH 2 — CH 3 (a)
(b) CH 3 — CH 2 — CH 2 — CH = CH — CH 3
(c) CH 3 — CH = CH — CH 2 — CH 2 — CH 3

(d) CH 2 = CH — CH 2 — CH 2 — CH 2 — CH 3

7. Me H Me (b)
Cl
H Cl

Me H
Cl
Hydrogenation of the above compound in the presence of (c)
poisoned palladium catalyst gives
(a) an optically active compound Cl
(b) an optically inactive compound
(c) a racemic mixture
(d) a diastereomeric mixture
HYDROCARBONS 181

H SO
13. HC º C - COOH ¾¾2 ¾¾
4® X
. The compound X is
Cl HgSO 4
(d)
(a) OHC.CH 2 .COOH (b) HOCH = CHCOOH
Cl Cl (c) both (a) and (b) (d) CH 2 = C(OH )COOH
11. Which of the following compounds are antiaromatic 14. Which of the following order is true regarding electrophilic
aromatic substitution of the three given compounds?

CH 3 CH 3 CH 3
O
– +
(I) (II) (III) (IV) (V) (VI)
CH 3
(a) (I) and (V) (b) (II) and (V)
CH 3
(c) (I) and (IV) (d) (III) and (VI) I II III

(a) II = III > I (b) II = III = I

(c) II >>> III > I (d) II >>> III = I
12. + HBr Z, Z is
15. A hydrocarbon with molecular formula C8H18 gives only
OH one monochloro derivative, on chlorination. The
compound is
Br (a) n-octane
Br
(b) iso-octane
(c) 2,2,4-trimethylpentane
(a) (b)
(d) 2,2,3,3-tetramethylbutane
OH OH

Br

(c) (d)

Br Br
 EBD_7374
182 CHEMISTRY

ANSW ER KEYS
Exercise 1 : Topic-wise MCQs
1 (c) 14 (c) 27 (b) 40 (d) 53 (a) 66 (a) 79 (b) 92 (a) 105 (c) 118 (a)
2 (c) 15 (d) 28 (d) 41 (d) 54 (c) 67 (d) 80 (b) 93 (a) 106 (b) 119 (d)
3 (d) 16 (c) 29 (a) 42 (b) 55 (b) 68 (b) 81 (a) 94 (a) 107 (d) 120 (a)
4 (d) 17 (b) 30 (a) 43 (c) 56 (b) 69 (a) 82 (c) 95 (a) 108 (c) 121 (c)
5 (a) 18 (b) 31 (d) 44 (a) 57 (a) 70 (c) 83 (d) 96 (a) 109 (b) 122 (c)
6 (c) 19 (c) 32 (b) 45 (c) 58 (a) 71 (d) 84 (c) 97 (c) 110 (a) 123 (d)
7 (b) 20 (b) 33 (a) 46 (d) 59 (a) 72 (c) 85 (a) 98 (c) 111 (d) 124 (d)
8 (a) 21 (b) 34 (c) 47 (c) 60 (d) 73 (b) 86 (b) 99 (c) 112 (c) 125 (c)
9 (d) 22 (a) 35 (c) 48 (d) 61 (a) 74 (c) 87 (d) 100 (c) 113 (b) 126 (d)
10 (d) 23 (c) 36 (d) 49 (c) 62 (c) 75 (c) 88 (b) 101 (d) 114 (a) 127 (a)
11 (a) 24 (b) 37 (c) 50 (a) 63 (b) 76 (d) 89 (b) 102 (a) 115 (b) 128 (b)
12 (b) 25 (b) 38 (a) 51 (d) 64 (c) 77 (a) 90 (b) 103 (a) 116 (a) 129 (b)
13 (c) 26 (a) 39 (b) 52 (b) 65 (b) 78 (b) 91 (b) 104 (a) 117 (d) 130 (a)
Exercis e 2 : Exemplar & Pas t Year MCQs
1 (d) 6 (d) 11 (b) 16 (a) 21 (a) 26 (d) 31 (d) 36 (c) 41 (c) 46 (c)
2 (a) 7 (c) 12 (c) 17 (b) 22 (b) 27 (a) 32 (d) 37 (c) 42 (c) 47 (d)
3 (b) 8 (b) 13 (c) 18 (c) 23 (d) 28 (a) 33 (c) 38 (d) 43 (a)
4 (a) 9 (d) 14 (c) 19 (d) 24 (d) 29 (d) 34 (c) 39 (c) 44 (b)
5 (a) 10 (c) 15 (c) 20 (a) 25 (c) 30 (d) 35 (a) 40 (d) 45 (d)
Exercis e 3 : Try If You Can
1 (c) 3 (b) 5 (d) 7 (b) 9 (d) 11 (d) 13 (c) 15 (d)
2 (a) 4 (b) 6 (a) 8 (b) 10 (c) 12 (b) 14 (d)